Iodoethane → 4(1H)-Pyridazinone, 1-ethyl-3,5-diphenyl-

HRID 597181Notes

Reaction equation

HRID 597181 reaction equation
[C:1]1([C:7]2[C:12](=[O:13])[C:11]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[CH:10][NH:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].[CH2:22](I)[CH3:23]>CN(C)C=O>[CH2:22]([N:9]1[CH:10]=[C:11]([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:12](=[O:13])[C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[N:8]1)[CH3:23]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 6192033,5-Diphenyl-1H-pyridazin-4-one

Product 1

HCID 122629914(1H)-Pyridazinone, 1-ethyl-3,5-diphenyl-

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A 1 g. portion of the product of Example 2 was suspended in 40 ml. of dimethylformamide, the suspension was cooled under nitrogen to 0°-5° C., and an 0.3 g. portion of 50% NaH in oil was added. The reaction mixture was stirred for 30 minutes, and 3 ml. of ethyl iodide was added. The mixture was stirred at 0°-5° C. for 24 hours, and the mixture was then filtered to separate the precipitated product. The dried product was 1.0 g. of 1-ethyl-3,5-diphenyl-4(1H)-pyridazinone, m.p. 124°-25° C., which was identified by nuclear magnetic resonance analysis, infrared analysis, and mass spectrometry.

Workup

  1. stirringThe mixture was stirred at 0°-5° C. for 24 hours
  2. filtrationthe mixture was then filtered
  3. customto separate the precipitated product

Sources & evidence

ORD record
ord-0b1b5d1c73a54f3789614da3bf4a634b
Source dataset
uspto-grants-1977_03
Patent number
US04013658

Reaction notes

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